This is charles igwe contribution on linolenic acid
molecular formular C18 H32 O2
Faty acid

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This is not exactly the target molecule. If you use NaNH2 to couple the ester you will end up with double addition to the ester instead of displacement of the bromine. Perhaps a Heck reaction with Heck reaction with Pd(OAc)2.
Bruce Bondurant
OMEGA LINOLENIC

Linonelic acid is a carboxylic acid with 18 - carbon chain and two cis double bond , the first double bond is located at the sixth carbon from the methyl end. It is an unsaturated n-6 fatty acid. It is a colorless liquid at room temperature. Linolenic acid is one of the two essential fatty acids that human and other animal must injest for good health

Thanks to Dr micheal Sabastin ( uf)
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Phelicia Slade




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http://pubs.acs.org/doi/abs/10.1021/jo00292a056
http://pubs.acs.org/doi/abs/10.1021/ja01154a029
Organic Chemistry Wade 6th ed.



3-bromo-1-propyne is added to 8-chloro-1-octyne, which forms 11-chloro 1,4 diundecyne . Next 1-bromo-2 – pentyne is added which should form 1-choloro (7,10,13) trihexadecyne. The process is completed with a malonic ester synthesis. Also a metal catalyst is used to complete the hydrogenation process of the fatty acid Linolenic acid.